Some tetrasubstituted organotin compounds are known from the prior art. For example, British Patent No. 966,813 to Ziegler discloses a method for obtaining tetrasubstituted organotin compounds useful as high polymers, but no suggestion is made in this patent that these compounds might find utility in controlling insects and other pests or be useful as herbicides and fungicides.
Other substituted organotin compounds are also known from the prior art for use as pesticides, acaricides bactericides, fungicides and herbicides or as protective coatings.
For example, U.S. Pat. No. 3,642,845 to Ramsden discloses bistrialkyltin compounds of the formula EQU (R).sub.3 SnR'Sn(R).sub.3
wherein R is an alkyl group and R' is a hydrocarbon di-radical having a minimum of 8 carbon atoms. These compounds exhibit systemic pesticidal activity, particularly against lepidoptera insect larvae, such as the Southern army worm.
Another example is U.S. Pat. No. 3,206,489 to Stamm et al. which discloses tetrasubstituted tin compounds of the general formula ##STR2## wherein R.sub.1, R.sub.2, and R.sub.3 and R.sub.4 can be alkyl radicals having from 1 to 12 carbon atoms and an aromatic hydrocarbon radical provided one of the R substituents is an alkyl radical terminating in a lower aliphatic thioacid group which is characterized by the presence of a thiocarboxyl function. These compounds are indicated as being useful as herbicides.
A further example in U.S. Pat. No. 3,591,614 to Bublitz which discloses compounds of the formula ##STR3## wherein R is 2-cyanoethyl, 2-carboxyethyl, or 2-carb(lower)alkoxyethyl group. These substituted ethyl derivatives of tricyclohexyltin are indicated as being useful as acaricides for the control of mites and ticks.
An additional U.S. Pat. No. 3,641,037 to Bublitz discloses compounds of the formula ##STR4## wherein R is 2-furyl, 2-pyridyl, 3-pyridyl, 1-indenyl, or 2-(2-pyridyl)ethyl, these compounds being useful as pesticides, particularly for the control of mites and ticks.
A further example is German patent No. 2,231,814 to Peterson which discloses compounds of the formula EQU (R).sub.3 SnCH.sub.2 -X
wherein X is alkyl- or arylsulfonyl, alkyl- or arylthio or dialkylamino and R is alkyl of from 1 to 14 carbon atoms. These compounds are disclosed as being useful in protective coatings against bacteria, fungi, termites and barnacles.
Peterson, in U.S. Pat. No. 3,725,446, claims some of the same compounds, R-S-CH.sub.2 -Sn-R.sub.3 ', where R is alkyl of from 1 to 14 carbon atoms, aryl or substituted aryl, and R' is alkyl of 1 to 14 carbon atoms. These compounds are said to have pre-emergent and post-emergent herbicidal activity.
Another German Patent No. 2,106,040 (U.S. Pat. No. 3,784,580 to Peterson) also discloses compounds of the formula (R).sub.3 SnCH.sub.2 -X wherein X is alkylsulfonyl, arylsulfonyl or dialkylsulfamoyl, the compounds being useful as pesticides and acaricides.
The compounds disclosed in the two German patents discussed immediately above differ from the compounds of this invention in that the "X" moiety is linked to the tin atom by a single methylene diradical instead of by a diradical having at least 2 carbon atoms.
Peterson has authored a paper, "Preparation and Reactions of some Sulfur-Substituted Tetraorganotin Compounds," J. Organometal Chem. 26, 215-223 (1971). The following paragraph appears at page 218:
"[(Phenylsulfonyl)methyl] tributyltin [(IV)] was found to be unreactive toward carbon dioxide and oxygen at room temperature, while exposure of a thin layer of (IV) to air resulted in ca. 50% decomposition to phenyl methyl sulfone and tributyltin oxide within four days. These findings, when regarded in conjunction, are in accord with hydrolysis being responsible for the air sensitivity of (IV)." PA1 X is (a) --SO.sub.2 R.sub.1, R' being hydrogen, and wherein R.sub.1 is a straight chain or branched alkyl having 1 to 18 carbon atoms, cyclohexyl, benzyl, phenyl or phenyl substituted with one or more groups which may be the same or different and which may be alkoxy having 1 to 8 carbon atoms, phenoxy, alkylthio having 1 to 8 carbon atoms, halogen, nitro, acetyl, acetamido, carboxy, alkoxycarbonyl, carbamoyl, cyano, hydroxy, trifluoromethyl, benzyl, naphthyl or norbornyl; naphthyl, biphenylyl, piperidinoethylmethiodide, --R.sub.2 Sn(CH.sub.3).sub.3 wherein R.sub.2 is polymethylene having from 2 to 11 carbon atoms, --R.sub.4 SO.sub.2 R.sub.5 Sn(CH.sub.3).sub.3 wherein R.sub.4 is ethylene and R.sub.5 is as defined for R.sub.2 above; PA1 (b) --OR.sub.7, R' being hydrogen, and wherein R.sub.7 is a straight chain or branched alkyl having 8 to 16 carbon atoms, aryl, alkoxyaryl, alkaryl, haloaryl, N,N-dialkylaminoalkyl, --R.sub.8 Sn(CH.sub.3).sub.3 wherein R.sub.8 is alkylene having 2 to 11 carbon atoms, cycloaliphatic having 4 to 6 carbon atoms, tetrahydro-1,1-dioxo-3-thienyl; PA1 (c) --SR.sub.10, R' being hydrogen, and wherein R.sub.10 is a straight chain or branched alkyl having 1 to 16 carbon atoms, phenyl, chlorophenyl, t-butylphenyl or --R.sub.2 Sn(CH.sub.3).sub.3 ; PA1 (d) --COR.sub.11, R' being hydrogen, and wherein R.sub.11 is --NHR.sub.12 wherein R.sub.12 is a straight chain or branched alkyl having 1 to 12 carbon atoms or aryl; --NHCH.sub.2 OH; --NHNH.sub.2 ; --NHCH.sub.2 NHCOR.sub.2 Sn(CH.sub.3).sub.3 ; --OR.sub.13 wherein R.sub.13 is a straight chain or branched alkyl having 8 to 15 carbon atoms; --(CH.sub.2).sub.m OH, wherein m is an integer from 2 to 4; --(CH.sub.2).sub.p N(R.sub.14).sub.2 wherein p is an integer from 2 to 4 and R.sub.14 is a straight chain or branched alkyl having 1 to 5 carbon atoms; --(CH.sub.2).sub.q OCOR.sub.2 Sn(CH.sub.3).sub.3 wherein q is as defined for p above; --(CH.sub.2).sub.s N.sup.+ (CH.sub.3).sub.3 I.sup.- wherein s is as defined for p above; PA1 (e) --NHCONH.sub.2, R' being hydrogen; PA1 (f) --NHCSNH.sub.2 ; R' being hydrogen; PA1 (g) 1-imidazolyl, R' being hydrogen; PA1 (h) N-2-oxopyrrolidinyl, R' being hydrogen; PA1 (i) --OCOR.sub.17, R' being hydrogen, and wherein R.sub.17 is --NHR.sub.18 wherein R.sub.18 is a straight chain or branched alkyl having 1 to 5 carbon atoms; 2-furyl; and --O(CH.sub.2).sub.t Sn(CH.sub.3).sub.3 wherein t is from 2 to 11; PA1 (j) --PO(OR.sub.20).sub.2, R' being hydrogen or ethoxy, and wherein R.sub.20 is a straight chain or branched alkyl having 1 to 5 carbon atoms; PA1 (k) tetrahydro-1,1-dioxo-2-thenyl, R' being hydroxyl; PA1 (l) --Si(OR.sub.21).sub.3, R' being hydrogen, and wherein R.sub.21 is a straight chain or branched alkyl having 1 to 5 carbon atoms; ##STR8## R' being hydrogen; (o) 2-pyridyl; PA1 (p) 4-pyridyl; PA1 (q) 2-alkyl-5-pyridyl; and n is an integer from 1 to 10. PA1 X is (a) --SO.sub.2 R.sub.1, R' being hydrogen, and wherein R.sub.1 is a straight chain or branched alkyl having 1 to 18 carbon atoms, cyclohexyl, benzyl, phenyl or phenyl substituted with one or more groups which may be the same or different and which may be linear or branched alkyl having 1 to 20 carbon atoms, cycloaliphatic having 4 to 6 carbon atoms, straight chain or branched alkenyl having 2 to 20 carbon atoms, alkoxy having 1 to 8 carbon atoms, phenoxy, alkylthio having 1 to 8 carbon atoms, halogen, nitro, acetyl, acetamido, carboxyl, alkoxycarbonyl, carbamoyl, cyano, hydroxy, trifluoromethyl, benzyl, naphthyl or norbornyl; naphthyl, biphenylyl, piperidinoethylmethiodide, --R.sub.2 Sn(CH.sub.3).sub.3 wherein R.sub.2 is polymethylene having from 2 to 11 carbon atoms, --R.sub.4 SO.sub.2 R.sub.5 Sn(CH.sub.3).sub.3 wherein R.sub.4 is ethylene and R.sub.5 is as defined for R.sub.2 above; PA1 (b) --OR.sub.7, wherein R.sub.7 is a straight chain or branched alkyl having 1 to 20 carbon atoms, haloalkyl, aryl, haloaryl, alkaryl, alkoxyaryl, epoxyalkylene wherein the alkylene group has 2 to 4 carbon atoms, N,N-dialkylaminoalkyl, tetrahydro-1,1-dioxo-3-thienyl, --R.sub.8 Sn(CH.sub.3).sub.3 wherein R.sub.8 is alkylene hving 2 to 11 carbon atoms, cycloaliphatic having 4 to 6 carbon atoms or aryl; PA1 (c) --SR.sub.10, R' being hydrogen, and wherein R.sub.10 is a straight chain or branched alkyl having 1 to 18 carbon agtoms, cyclohexyl, benzyl, phenyl or phenyl substituted with one or more groups which may be the same or different and which may be linear or branched alkyl having 1 to 20 carbon atoms, cycloaliphatic having 4 to 6 carbon atoms, straight chain or branched alkenyl having 2 to 20 carbon atoms, alkoxy having 1 to 8 carbon atoms, alkylthio having 1 to 8 carbon atoms, halogen, nitro, acetyl, acetamido, carboxyl, alkoxycarbonyl, carbamoyl, cyano, hydroxy, trifluoromethyl, benzyl, naphthyl or norbornyl; naphthyl, biphenylyl, piperidinoethylmethiodide, --R.sub.2 Sn(CH.sub.3).sub.3 wherein R.sub.2 is polymethylene having from 2 to 11 carbon atoms, --R.sub.4 SO.sub.2 R.sub.5 Sn(CH.sub.3).sub.3 wherein R.sub.4 is ethylene and R.sub.5 is as defined for R.sub.2 above; PA1 (d) --COR.sub.11, wherein R.sub.11 is --NH.sub.2, --NHNH.sub.2, --NHCH.sub.2 OH, --NHR.sub.12 wherein R.sub.12 is a straight chain or branched alkyl having 1 to 12 carbon atoms or aryl; --NHCH.sub.2 NHCOR.sub.2 SN(CH.sub.3).sub.3, --OR.sub.13 wherein R.sub.13 is a straight chain or branched alkyl having 1 to 15 carbon atoms, --(CH.sub.2).sub.m OH wherein m is an integer from 2 to 4, --(CH.sub.2).sub.p N(R.sub.14).sub.2 wherein p is an integer from 2 to 4 and R.sub.14 is a straight chain or branched alkyl having 1 to 5 carbon atoms, --(CH.sub.2).sub.q OCOR.sub.2 Sn(CH.sub.3).sub.3 wherein q is as defined for p above, --(CH.sub.2).sub.s N.sup..sym. (CH.sub.3).sub.3 I.sup..crclbar. wherein s is as defined for p above; PA1 (e) --NHCONH.sub.2 ; PA1 (f) --NHCSNH.sub.2 ; PA1 (g) 2-pyridyl; PA1 (h) 4-pyridyl; PA1 (i) 2-alkyl-5-pyridyl; PA1 (j) 9-carbazolyl; PA1 (k) 1 -imidazolyl; PA1 (l) N-2-oxopyrrolidinyl; PA1 (m) --OCOR.sub.17, wherein R.sub.17 is --NHR.sub.18 wherein R.sub.18 is a straight chain or branched alkyl having 1 to 5 carbon atoms or aryl; 2-furyl; and --O(CH.sub.2).sub.t Sn(CH.sub.3).sub.3 wherein t is an integer from 2 to 11; PA1 (n) --PO(OR.sub.20).sub.2 wherein R.sub.20 is a straight chain or branched alkyl having 1 to 5 carbon atoms; PA1 (o) tetrahydro-1,1-dioxo-2-thenyl; PA1 (p) --Si(OR.sub.21).sub.3 wherein R.sub.21 is a straight chain or branched alkyl having 1 to 5 carbon atoms; ##STR11## n is an integer from 1 to 10. PA1 K. hayashi, J. Iyoda and I. Shiihara, J. Organometal. Chem., 10, 81 (1967). PA1 H. g. kuivila, Advan. Organometal Chem., 1, 47 (1964). PA1 W. p. neumann, Angew. Chem., Internat. Edit., 2, 165 (1963).
Peterson, in U.S. Pat. No. 3,794,670, has covered a method for preparing (organosulfonylmethyl) triorganotin compounds by reacting a triorganotin amine and an organosulfonylmethyl compound.
Ayrey et al. have published a paper, J. Organometal. Chem. 35, 105-109 (1972), in which they deal with the preparation of 3-(trialkylstannyl)propyl aryl sulfides, R.sub.3 SnCH.sub.2 CH.sub.2 CH.sub.2 SR'. No utility is stated for these compounds.
Koopmans, in U.S. Pat. No. 3,031,483, discloses compounds of the structure ##STR5## in which R.sub.1, R.sub.2 and R.sub.3 may be the same or different and represent alkyl groups with 1-12 carbon atoms, phenyl groups or halophenyl groups, and Q represents one of a number of groups, including ##STR6## These compounds have fungicidal and bactericidal properties.